Each of these reactants is a chiral molecule because their mirror images are nonsuperimposible. this is wrong - talk to me at a workshop before the exam to make sure you understand how to tell chirality
However, only one of the reactants, 2-[(tert-butoxycarbonyl)amino]-4-(methylthio)butanoic acid contains a chiral center. Having a chiral center is not the only factor of a chiral compound, for example the other reactants could have axial or planar chirality.
The chiral center in 2-[(tert-butoxycarbonyl)amino]-4-(methylthio)butanoic acid is the 2nd carbon, which is bonded to HOCO, H, tert-butoxycaronylamino, and CH2CH2SCH3. Because the compound has only one chiral center, it is chiral. true
The product of the reaction, the diketopiperazine, contains 2 chiral centers. A compound with more than one chiral center may or may not be chiral. Also, because the molecule has 2 chiral centers, it should have 4 stereoisomers, following the 2^n rule. The stereoisomers could be enantiomers or diastereomers, which are not mirror images. true
Chirality in Ugi synthesis
Experiment 14 (you should have linked to the experiment not the blog main page) is the Ugi synthesis and cyclization to a diketopiperazine using phenylacetaldehyde, 5-methylfurfurylamine, N-(tert)butoxycarboyl L-methionine, and benzylisocyanide.
phenylacetaldehyde
(5-methyl-2-furyl)methylamine
2-[(tert-butoxycarbonyl)amino]-4-(methylthio)butanoic acid
Benzyl isocyanide
pics not showing up
Each of these reactants is a chiral molecule because their mirror images are nonsuperimposible.
this is wrong - talk to me at a workshop before the exam to make sure you understand how to tell chirality
However, only one of the reactants, 2-[(tert-butoxycarbonyl)amino]-4-(methylthio)butanoic acid contains a chiral center. Having a chiral center is not the only factor of a chiral compound, for example the other reactants could have axial or planar chirality.
The chiral center in 2-[(tert-butoxycarbonyl)amino]-4-(methylthio)butanoic acid is the 2nd carbon, which is bonded to HOCO, H, tert-butoxycaronylamino, and CH2CH2SCH3. Because the compound has only one chiral center, it is chiral.
true
The product of the reaction, the diketopiperazine, contains 2 chiral centers. A compound with more than one chiral center may or may not be chiral. Also, because the molecule has 2 chiral centers, it should have 4 stereoisomers, following the 2^n rule. The stereoisomers could be enantiomers or diastereomers, which are not mirror images.
true
diketopiperazine
4/10